Local anaesthetic



fatented Aug. 4, 1931 UNITED STATES HARVEY o. BRILL, orCAMBRIDGE,-;MASSA.GHUSET'J1S. I

LOCAL enzssr ris'rrc' g No Drawing.

This invention relates to local anaesthetics. I have found that thearomatic esters of the general formula B 000 N X ll a Y in which B maybe any aromatic radical, a, b, 0 and d may be either hydrogen atoms or walkyl radicals, n the number of carbon atoms in the chain, X an alkylradical containing Application filed October 1, 19 281 "Serial"na'soaeas;

four or more carbon atoms, and Y either a methyl or ethyl radical,possess local anaesthetic action similar to cocaine and are devoid ofthe narcotic action of cocaine. To avoid repetition of expression,whenever hereinafter the language member of the above series, or membersof the above series is used, it will be understood that the generalformula,

a O moood-d N l in with its concomitant meanings, as outlined, will bereferred to.

The members of the above series are, 1n general, colorless compounds,011s or lowmelting solids, little soluble 1n Water, more readily solublein alcohol or ether, of alkaline reaction to litmus, decomposed uponheating with acids or alkalies into the component aromatic acid andamino-alcohol, and capable of forming salts with acids. Both the estersand their salts have the property of producing local anaesthesia similarto cocaine.

To prepare a member of the above serles, the process may be carried out,for instance, as follows:

parts, by weight, of beta-normal butyl ethyl aminoethanol are dissolvedin 10 parts,

aqueous solution=of this -salt,;sl0clium carbonate liberates thefireeibase, namely, the oinnamic esterof beta-normal butylethylaminoethanol, -as :a colorless, low-melting solid, little soluble inwater, more readily soluble in alcohol or ether, of alkaline reac tion:totlitmus, decomposed upon heating with 1 sodlum hydroxide into sodiumcinnamate and in which R comprises a cinnamic acid, a, b, c and all maybe, either hydrogen atoms or alkyl radicals, n a whole number signifyingthe number of carbon atoms disposed in the chain, X an alkyl radicalcontaining four or more carbon atoms, and Y either a methyl or ethylradical, being, in general, colorless compounds, oils or low-meltingsolids, little soluble in water, more readily soluble in alcohol orether, of alkaline reaction to litmus, decomposed upon heating withacids or alkalies into the component aromatic acid and amino-alcohol,capable of forming salts with acids, from which salts the free base isliberated by means of sodium carbonate, and having the property ofproducing local anaesthesia similar to cocaine, yet devoid of thenarcotic action of cocaine.

2. As a new product, the cinnamic ester of beta-normal butyl ethylaminoethanol, being a colorless compound, little soluble in water, morereadily soluble in alcohol or ether, of alkaline reaction to litmus,decomposed upon heating with sodium hydroxide into sodium cinnamate andbeta-normal butyl ethyl aminoethanol, capable of forming a hydrochloridemelting at 151 C., from the aqueous solution of which salt the freebase, namely, the cinnamic ester of beta-normal butyl ethylaminoethanol, is liberated as a colorless, lowmelting solid by means ofsodium carbonate, and having the property of producing local anaesthesiasimilar to cocaine, yet devoid of the narcotic action of cocaine andhaving the following probable formula:

my name.

HARVEY C. BRILL.

